Cadmium compounds of the acridin series, and a process of making the same.



cAD nIUMcoMroUNns or THE ACRIDIN=SER1ES; AND nrnoonss or Mannie mam a No Drawing.

UNITED sT aEs PATENT OFFICE.

1 am. HttssYAnD anna -N, or nasnn, SWITZERLAND. ASSIGNORSTO socIE'rYi" or CHEMICAL mnus'rmgrn asra, or" BASEL,-SWITZEBLAND.

i To all whom it may concern:

' Be known thatwe, Paul. Hussy, physician, and MAX HARTMANN, chemist, both citizens of the SWissRe p ublic, and residents of Basel, Switzerland, have invented new and useful Cadmium Compounds of the Acridin Series, and a Process of Making the Same, of which the following is a, full, clear,

' and exact specification.

\Ve have found that therapeutically valuable disinfectants ofthe acridin series are obtained acting with a soluble cadmium salt, on corresponding quantities of the bases or salts of acridin dyestuffs, which may be alkylated at the acridin nitrogen, in presence of a convenient solvent, as for instance upon the crystallization of the cadmium compound formed begins mostly after a short time and can be "completed by cooling or, if desired, by adding a convenient precipitant, as, for instance, ether. The separation of the new compounds 'isfelfected in the usual manner by filtering, washing and drying.

The new disinfectants constitute red to brown powders, which dissolve in water to orange-yellow to red-brown solutions, in alcohol, acetic ether, glacial acetic acid-and "acetone to solutions showing after dilution yellow-green fluorescences and in concen trated sulfuric acid 'with an intense green;- Even when greatly diluted, their solutions still strongly, act on bacteria to check the" growth thereof. 7 a

The process is illustrated by the follow ng examples Example 1: 335 gr. of the hydrochlorate of the acridin dye'stuif methylated at the acridin' nitrogen, obtained in the known manner by heating 2:7-dimethyl-3:6-d1aminoacridin with methyl chlorid under pressure, are dissolved in a little hot water and to the obtained solution is added a solution of 188 gr. of cadmium chlorid in hot water. The new cadmium compound separates 1m- Specification of Letters Patent. Pate nted'Jull' 5, 19 i i ,A- Application filed Apri17,1917. Seria1'No.160,556.

niediately as lumps which 'disintegi a tefby friction to tile-red crystals. "The produ'cti's "dried by suction, washed with 'alcolroh'and ether and dried. It constitutes tile-red powder soluble 111 water with alibi-angeyellow coloration an'din'concentrated sulfu'ric acid with a green fluorescence.

Example 2: To 12 parts of 3:6-diamino-i acridin suspended in a little hot water is added hydrochloric acid until the mass shows with Congo a feeble acid reaction. In the ,solution of 3:6-diaminoacridin hydrochloratefis then poured a hot solution 0M5 parts crystallizedcadmium chlorid ina little water. The separation of the newbrown cadmium compound begins immediately. After standing for several hours it is isolated by filtration and suction, washed with a mixture of alcohol and ether and dried in an exsicca'tor. It constitutes a brown powder, soluble' in water with a 'ellow-grccn fluorescence, in alcohol to a red-brown solution showing also after dilution a. green fluorescence, and in sulfuric acid with a brown-green fluorescence and insoluble in ether, chloroform and benzene.

Example 3;; $7 parts of the acri din dyestulf corresponding to the formula are dissolved in parts of hot alcohol containing 3 parts of concentrated hydrochloric acid, To the filtered solutionlarnpadded 4.4 parts of crystallized .cadmfiiin' ch-lorid dissolved in 20 parts of alcohol ancltlie mass is let to cool. After standing for lflthours. the separated crystals are filtered ofl'. dried by suction and washed first 'with a little alcohol and afterward with-ether and dried in an exsiccator. The obtained product is a deepbrown powder dissolving in water to a redbrown solution showing after dilution :1 yellmv-green fluorescence, likewise in alcohol, in sulfuric acid with a yellmv-grtwyn fluorescence and insoluble in ether, chlor'o;

form and benzene.

Instead of those indicated in the eicam les, other acridin dyestuffs can be transormed into cadmium compounds showing analogous properties. For the cadmium chlorid emplo d in the examples other convenient cadmium compounds can be employed. Also the other conditions may be varied within wide limits.

What we claim is:

1.,The herein described process for the manufacture of cadmium compounds of the acridin series, consisting in acting on an acridin dyestufi with a soluble cadmium salt in presence of a solvent. 2. The described process for the manufacture of cadmium compounds of the acridin series, vconsisting in acting on an acridin dy estuff alkylated at the acridin nitrogen with-a soluble cadmium salt, in presence of asolvent.

3. As a new product, the herein described cadmium compounds of the acridin series,

constituting red to brown powders, soluble in water-with orange-yellow colorations, alcohol, acetic ether, glacial acetic acid and acetone to solutions showing after dilution a yellow-green fluorescence and in concentrated sulfuric acid with an intense green fluorescence.

. 4. As a new article of manufacture, the herein described cadmium compound of the 2 :7 4 dimethyl 3 :6 diamidoacridin, methylated at the acridin nitrogen, which constitutes a tile-red powder soluble in water with orange-yellow coloration, in alcohol, acetic ether, glacial acetic acid and acetone with a yellow-green fluorescence and in concentrated sulfuric acid with a green fluores- I cence.

In witness whereof we have hereunto signed our names this sixth day of March, 1917, in the presence oftwo subscribing witnesses.

PAUL HUSSY. MAX HARTMANN.

Witnesses:

CARL O. SPAMER, LYDIA UEBELE. 

